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[ CAS No. 50593-92-5 ] {[proInfo.proName]}

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Chemical Structure| 50593-92-5
Chemical Structure| 50593-92-5
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Product Details of [ 50593-92-5 ]

CAS No. :50593-92-5 MDL No. :MFCD00238866
Formula : C6H5BrN2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :YJEWVVYJOJJLBP-UHFFFAOYSA-N
M.W : 249.09 Pubchem ID :291786
Synonyms :

Calculated chemistry of [ 50593-92-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.41
TPSA : 88.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 1.66
Log Po/w (MLOGP) : 0.59
Log Po/w (SILICOS-IT) : 1.52
Consensus Log Po/w : 1.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.63
Solubility : 0.583 mg/ml ; 0.00234 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.213 mg/ml ; 0.000856 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.38
Solubility : 1.03 mg/ml ; 0.00415 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 50593-92-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 50593-92-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 50593-92-5 ]
  • Downstream synthetic route of [ 50593-92-5 ]

[ 50593-92-5 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 50593-92-5 ]
  • [ 31462-59-6 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 3129
  • 2
  • [ 50593-92-5 ]
  • [ 100-52-7 ]
  • [ 14001-67-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 2, p. 219 - 224
  • 3
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  • [ 14001-67-3 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 3129
  • 4
  • [ 50593-92-5 ]
  • [ 1126-44-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1374 - 1380
[2] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1986, vol. 40, # 7, p. 588 - 592
[3] Journal of the Chemical Society, 1953, p. 3129
[4] Patent: WO2006/117368, 2006, A1, . Location in patent: Page/Page column 46
  • 5
  • [ 50593-92-5 ]
  • [ 1126-44-9 ]
Reference: [1] Patent: US2003/119811, 2003, A1,
  • 6
  • [ 488-11-9 ]
  • [ 867-44-7 ]
  • [ 50593-92-5 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With triethylamine In water at 10 - 20℃; for 28 h;
Stage #2: With hydrogenchloride In water
Mucobromic acid (58.05 g, 0.225 mol) was added to a stirred solution of 2-methyl-2-thio- pseudourea sulfate (62.66 g, 0.225 mol) in water (500 mL) at r.t. The suspension was cooled to 10 °C (ice bath) and triethylamine (94.1 mL, 0.675 mol) was added dropwise over 4 h. The reaction mixture was then left to stand at r.t. for 24 h. Activated carbon (Darco G-60) was added to the now dark red / brown solution and after stirring for 10 min the charcoal was filtered off. The filtrate was acidified with concentrated hydrochloric acid (50 mL) and the yellow precipitate was filtered off, washed with water (2 x 80 mL) and diethyl ether (2 x 100 mL), and then placed in a vacuum oven at 50 0C for 2 days to yield 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (33.13 g, 59percent) as a yellow amorphous solid. 1H NMR δ (de-DMSO, 400 MHz) 2.75 (s, 3 H), 9.20 (s, 1 H).
45% With triethylamine In water at 10 - 20℃; for 13 h; (Z)-2 , 3-d ibromo-4- oxobut-2-enoic acid (30 g, 0.116 mol) was added to a stirred solution of methyl carbamimidothioate sulfate (1.2) (32 g, 0.116 mol) in water (250 mL) at it The suspension was cooled to 10 °C (ice bath) and Et3N (48.6 mL, 0.349 mol) was addeddrop wise over 1 h. The reaction mixture was stirred at rt for 12 h. Activated carbon (10 g) was added to the now dark reddish solution and 10 mm later, the charcoal was filtered off. The filtrate was acidified with concentrated hydrochloric acid (25 mL) and the yellow precipitate was filtered off, washed with water (2 x 80 mL) and diethyl ether (2 x 100 mL), dried in vacuum to afford the title compound (13 g, 45percent yield) as a yellow solid. LC-MS:[M-H] 247.7.
Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 2, p. 539 - 547
[2] Patent: WO2006/66172, 2006, A1, . Location in patent: Page/Page column 50
[3] Patent: WO2017/221100, 2017, A1, . Location in patent: Paragraph 00283
[4] Patent: WO2014/99836, 2014, A1, . Location in patent: Page/Page column 29; 30
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YieldReaction ConditionsOperation in experiment
55% With triethylamine In water at 0℃; Mucobromic acid (300 g, 1.16 mol) was added to an aqueous solution (2.5 L) of 2-methyl-2-pseudothiourea sulfate (324 g, 1.16 mol) at room temperature. The resultant suspension was cooled to 0°C with stir, and triethylamine (486 mL, 3.49 mol) was added dropwise thereto over four hours. The resultant reaction mixture was stirred overnight, and the completion of the reaction was confirmed by silica gel TLC. The reaction mixture was then acidified with concentrated hydrochloric acid (about 250 mL). The resultant yellow solid was collected by filtration and washed twice with water (500 mL) and then twice with diethyl ether (500 mL). The solid was dried under reduced pressure to yield the title compound (160 g, 55percent).
Reference: [1] Patent: EP3305785, 2018, A1, . Location in patent: Paragraph 0165; 0166
  • 8
  • [ 488-11-9 ]
  • [ 2986-19-8 ]
  • [ 50593-92-5 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 13, p. 2231 - 2241
[2] Patent: WO2006/117368, 2006, A1, . Location in patent: Page/Page column 45-46
  • 9
  • [ 90994-06-2 ]
  • [ 4338-95-8 ]
  • [ 50593-92-5 ]
Reference: [1] Patent: WO2007/88014, 2007, A1, . Location in patent: Page/Page column 30-31
  • 10
  • [ 488-11-9 ]
  • [ 14527-26-5 ]
  • [ 50593-92-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2215 - 2226
  • 11
  • [ 50593-92-5 ]
  • [ 7758-99-8 ]
  • [ 100130-05-0 ]
Reference: [1] Patent: US5707989, 1998, A,
[2] Patent: US5821240, 1998, A,
[3] Patent: US5977102, 1999, A,
  • 12
  • [ 50593-92-5 ]
  • [ 100130-05-0 ]
Reference: [1] Canadian Journal of Chemistry, 1956, vol. 34, p. 1444
  • 13
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  • [ 98550-19-7 ]
Reference: [1] Patent: US5821240, 1998, A,
[2] Patent: US5821240, 1998, A,
[3] Patent: US5977102, 1999, A,
  • 14
  • [ 67-56-1 ]
  • [ 50593-92-5 ]
  • [ 50593-91-4 ]
YieldReaction ConditionsOperation in experiment
80% for 24 h; Reflux Preparation 30: Methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate A solution of 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (7.64 g, 30.7 mmol) in MeOH (60 mL) was treated with sulfuric acid (2 mL) and boiled for 24 hours. The mixture was poured onto ice water and extracted with DCM. The DCM phase was washed with saturated aqueous sodium hydrogen carbonate solution, dried and evaporated to give the title compound (6.42 g, 80percent). 1 H NMR (500 MHz, CDCI3): δ 8.72 (s, 1 H), 4.01 (s, 3H), 2.58 (s, 3H). LCMS (ESI) Rt = 2.35 minutes 263 [M+H]+
80% for 24 h; Reflux Preparation 29 (1052) Methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate (1053) A solution of 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (7.64 g, 30.7 mmol) in MeOH (60 ml_) was treated with sulfuric acid (2 ml_) and heated to reflux for 24 hours. The mixture was poured onto ice water and extracted with DCM. The organic layer was washed with saturated aqueous NaHC03, dried (MgS04) and concentrated in vacuo to afford the title compound (6.42 g, (1054) 80percent). (1055) 1 H NMR (500 MHz, CDCb): δ ppm 8.72 (s, 1 H), 4.01 (s, 3H), 2.58 (s, 3H). LCMS (ESI) Rt = 2.35 minutes, MS m/z 263 [M+H]+
79% at 0 - 85℃; for 1 h; Th ion ly chloride (3.1 mL, 43.8 mmol) was added dropwise to 5-bromo-2-(methylthio)pyrimidine-4- carboxylic acid (1.3) (5.5 g, 22.2 mmoL) in methanol (50 mL) at 0 °C. The resultingmixture was stirred at 85 °C for 1 h, cooled to rt, and then poured into aq. NaHCO3 solution (100 mL). The mixture was extracted with CH2CI2 (3 x 100 mL). washed with water (50 mL), brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was recrystallized from petroleum ether to afford the title compound (4.6 g, 79percentyield) as a yellow solid. LC-MS: [MH] = 262.7.
75% at 0℃; Reflux A solution of 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (110 g, 0.44 mol) in methanol (1.1 L) was cooled to 0°C with stir, and thionyl chloride (50 mL, 0.66 mol) was added dropwise thereto. The resultant reaction mixture was slowly heated, and the reaction was allowed to proceed under reflux for four hours. The completion of the reaction was confirmed by LC/MS and TLC, and the reaction mixture was cooled to room temperature. The volatiles were removed through evaporation under reduced pressure, and the residue was dissolved in ethyl acetate (1 L). The resultant solution was washed three times with 10percent aqueous sodium carbonate solution (200 mL) and then twice with saturated brine (200 mL). The resultant organic phase was dried over anhydrous magnesium sulfate, and solid was separated by filtration. The filtrate was then concentrated under reduced pressure, and the resultant crude product was purified by silica gel column chromatography to yield the title compound (88 g, 75percent).

Reference: [1] Patent: WO2014/37750, 2014, A1, . Location in patent: Paragraph 00149; 0046-0050
[2] Patent: WO2015/128676, 2015, A1, . Location in patent: Page/Page column 117-118
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2215 - 2226
[4] Patent: WO2017/221100, 2017, A1, . Location in patent: Paragraph 00284
[5] Patent: EP3305785, 2018, A1, . Location in patent: Paragraph 0167; 0168
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  • [ 50593-92-5 ]
  • [ 50593-91-4 ]
Reference: [1] Patent: WO2007/88014, 2007, A1, . Location in patent: Page/Page column 31
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1687 - 1691
  • 16
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 1, p. 114 - 120
  • 17
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  • [ 30321-94-9 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 13, p. 2231 - 2241
  • 18
  • [ 50593-92-5 ]
  • [ 90905-31-0 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1986, vol. 40, # 7, p. 588 - 592
  • 19
  • [ 50593-92-5 ]
  • [ 64-17-5 ]
  • [ 74840-38-3 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 2, p. 539 - 547
  • 20
  • [ 50593-92-5 ]
  • [ 102921-92-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1374 - 1380
[2] Patent: WO2006/117368, 2006, A1,
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